Sam Bear Sounds Off on the Santa Barbara Comedy Scene

Samantha Bearman, also known as Sam Bear, describes herself as a “multi-preneur” — a multi-faceted entrepreneur — and embodies many roles, the first of which is the owner of Bear Cave Comedy. These comedy shows showcase comedians who have been featured on NBC and Conan and are viral sensations on social media, along with Bearman’s own comedy, in an array of creatively themed events across the city.

Bearman, who has lived mostly in Santa Barbara since 1988, is a queer Latinx community leader, professional comedy and lifestyle coach, writer, podcaster, and more, who throughout the COVID pandemic helped to keep Santa Barbara’s colorful comedy scene not only alive, but thriving. She shares some of her journey as a comedy trailblazer.

What originally inspired you to step into the world of comedy? What originally inspired me to step into the world of comedy has to be a combination of several factors. First and foremost, I would be remiss if I didn’t mention that my father has very proudly, throughout the entirety of my life, always proclaimed that he was voted “wittiest boy” of his graduating class — a long-held title of honor in my family’s house growing up.

Additionally, I’m blessed to have two parents who are incredible public speakers and always made sure that their children witnessed them speaking to large rooms filled with people and small rooms with intimate attendance. I was able to see firsthand how to control a room, how to inspire the energy that you want in your audience, and how to use my voice, pauses, and my body language to communicate and emphasize a story.

Which comedians’ work do you admire? A comic who I really respect is Gabriel Iglesias. I’ve seen him perform four different times, and it’s impressive because he is a clean comic, and the way that he tells his jokes has such a genuine storytelling sensation. It feels like you’re on the phone with a friend and they’re catching you up on their life.

I’m also a huge fan of Gina Brillon. After seeing her on America’s Got Talent, I rushed to social media to make sure that I could follow her. In her comedy, there is a raw and honest quality. That point of view in her writing, which I believe comics strive to achieve, when you see it unfolding before you … it is aspirational. And it also makes you question if anything that you’ve written today is truly as vulnerable as what you’re seeing perform before you on stage.

What draws you to comedy? Do you think comedy lends itself well to delivering certain messages? I love the storytelling aspect of comedy and the truth-telling that’s behind it — the unique ability to share moments that have happened in our lives that, at the time, may have completely wrecked us and destroyed the version of life that we were living.

For a comedian to be able to take some of the hardest moments of their life and turn it around into a story that connects with other human beings as a sometimes teachable moment, or a moment to look at and say the universe and the world are so beautifully chaotic. Can you believe that this thing I thought only happened to me has actually happened over and over and over again in our history?

What was your experience like the first times that you did stand up comedy? How have your sets evolved? The first time I did stand-up comedy I was incredibly underprepared and did not really understand all that goes into a solid set. The first time I did a set that I took very seriously, I was very nervous. My heart was pounding so fast, but I had a huge smile on my face. My family was sitting in the front with my roommate, and right before I went on, I remember thinking, “Oh my God, I hope they all laugh!”

My sets definitely evolved over time. I had to continue to find my voice and I still feel like I’m out of place, but I’m much closer to pinpointing exactly the point of view that I want to infuse into all of my humor.

Tell us about your experiences competing in comedy events. So I was definitely thrust into competing for Jimmy Kimmel’s funniest college student in America. I was in college. The day of that show, I was actually running the event … I was really excited to be that close, but I was working, so I didn’t even think I was allowed to submit. Well, my boss showed up, saying she’d spoken with their staff, and I was good to go! I immediately felt out of place.

I clearly was looking uncomfortable because a senior walked up to me with confidence and an effortless cool that was incredibly intimidating, and said to me, “You look really nervous.”

As the tears started to well in my eyes, he sat down next to me and said, “I want to tell you something — I know you’re funny.”

I said, “How could you know that?” and he said, “I know you’re funny because you wouldn’t be sitting here if you didn’t know you were funny, if some part of you didn’t wholeheartedly believe in the truth that you are funny. I’m going to let you in on a little secret — the audience wants to laugh. They don’t want to see you fail — it’s uncomfortable seeing somebody fail. The audience knows that they have a job. Their job is to be open to laughter. Now your job is to get them to laugh.”

I took to the stage, and guess what people did — they laughed. I had a lot of fun…. Maybe I didn’t win, but that certainly felt like a win to me.

You cover topics like “millennial dating, sex, family, and how you can have a master’s degree, professional career, and three side hustles and still not be able to afford sand on the beach.” Can you elaborate on these topics and themes that come up in your sets? As a millennial comic, I absolutely couldn’t get away without addressing what dating as a millennial is like, especially considering the fact that most people who condemn millennials seem to think that we are a generation that never ages, despite the fact that the youngest millennial is 35 years old. However, we were probably the last generation that had a mix of meeting people organically while also being the first to test out dating websites and apps.

And honestly, sex is funny. I’m actually writing a book called I Didn’t Know You Could Laugh During Sex, which includes submissions from people on comical moments they experienced while getting down and dirty.

Living in one of the most beautiful places in the world but not actually being able to afford to live here — this is something that becomes more and more relatable to people. To put it bluntly, I talk about how living in Santa Barbara is one of the most challenging things that I’ve had to do, and I think it also brings light to the reality of the rental market and the housing market right now.

With Bear Cave Comedy, what was it like temporarily being the only comedy experience in operation during the pandemic in Santa Barbara? Holding down the comedy scene temporarily was pretty exciting as a brand-new business. … I think we were all working to navigate what this world looked like and how we could participate in it and still hopefully create and find some joy for ourselves and others. I really enjoyed the opportunity to explore different kinds of shows.

Keep in mind, during the time when I believed Bear Cave Comedy was the only comedy option, this was back when everything was still online, so creativity really had to evolve. Through being temporarily the only comedy option, I was able to create a variety of different online comedy packages which I still do today.

What originally inspired you to create Bear Cave Comedy? As I continued to pursue comedy and performed in more shows, I quickly noticed that most comedy shows tend to lean more toward all-male lineups, and the struggle for a woman of color is tenfold harder. There is so much gatekeeping within the comedy industry. It feels like the wild, wild west, with simultaneously no rules, and yet inundated with a myriad of unspoken rules that are frankly outdated.

I used to walk past buildings for rent and dream about what my comedy club would look like. I knew the name of it immediately: “The Bear Cave.” It took about a year of walking past empty buildings for me to realize that I was building a story around a limiting belief that I created — that I was not able to run a comedy business without a brick and mortar. So, armed with a newfound sense of determination and ambition, I began searching for venues where female comics could have their own space to share their talents without having to compromise or settle for second-class status.

The moment I shifted gears and opened my eyes up to a different way of accomplishing the same goal, opportunities began to present themselves. In the words of my mother, “Risk is the price of admission.”

What does the creative process look like coming up with the different shows? The creative process of coming up with different shows is a beautiful combination of a love for alliteration and looking at the space and venue that I’ll be utilizing as a pop-up-style show. I like things to be a little tongue-in-cheek, which is why my show that combines comedians and drag performers is called “Comedy Is a Drag,” and of course “Puff, Puff, Laugh” was inspired by the fact that it’s the only show that takes place at your CBD store in Santa Barbara… So far!

What do your shows entail? Each of my shows are slightly different. We do have what I would categorize as traditional comedy shows, which are a series of comedians on a lineup rounding out with either a feature and a headliner, or just a headliner. However, we also have some themed shows, which I absolutely love.

We currently have the token comedy show, where the entire lineup is made up of female comedians or non-binary comedians, except for one token male comedian on the show … designed as a way to bring awareness and attention through a creative manner to the inequitable representation of women and non-binary comics on traditional comedy shows which tend to only tokenize those performers by having one, maybe two, on a show.

If I have a full comedy show that is only female comics, it is not marketed as a “ladies night” or “ladies only.” I’m also a huge fan of drag as a performance, and I was thrilled by the hybrid union of my theme show, “Comedy Is a Drag,” where we have comedians, drag kings, and drag queens all performing in the same show.

At most of my Bear Cave comedy shows, you will see me perform on stage … and there have been instances where I have stepped in as the headliner.

Any big plans for the future? Personally, I would love to film and release my own comedy special, the title being Hurry Up and Get Famous. I also am releasing a co-authored book in the next several months all about women entrepreneurs and creatives, titled The Future of Entrepreneurship Women Who Lead, available on Amazon Kindle in October.

I also want to say if there’s anyone who wants to try comedy, go for it. Don’t listen to anybody who tells you you’re not good enough or that it’s embarrassing. Go after it, go to an open mic and put your name on the list and give it your best shot for three minutes.

It’s the greatest rush, and the most amazing superpower to make people laugh. 

For more information, see bearcavecomedy.com.